UPDATE: Please note, that Microsoft since then has updated its support policies to grant an extended 30 months support for all 09 Feature Updates and the regular 18 months for all 03 Feature Updates.

Have you seen Microsoft's recent announcements to extend support for an additional six months for all enterprise and educational customers who are on Windows 10 version 1511, 1607, 1703, and 1709 to give them more time to figure out their upgrade logistics?

Version 1607 Was To Expire Before Version 1511

Before we start, a little background. Michael Niehaus, Microsoft's former Director of Product Marketing for Commercial Windows, announced on November 14th, 2017 that the company will provide its enterprise and education customers currently on version 1511 with continuing "updates to address critical and important security issues" for an additional six months. This is done "to help some early enterprise adopters that are still finishing their transition to Windows as a service."

On March 13th, 2018, the next feature update version 1803 code-named Redstone 4 and rumored to be called "Spring Creators Update" is supposed to be released. On April 10th 2018 (that month's Patch Tuesday) or shortly after, the November Update (1511), will have reached its official end of support after 29 months of support.

This put Microsoft in an awkward position: Version 1607, the so-called Anniversary Update, was released about eight months AFTER 1511 but was set to expire BEFORE 1511 on or shortly after March 13th, 2018 depending on when the company releases Redstone 4 — giving customers on this version 20 months of support.

Microsoft had several options at this point:

They could choose to do nothing.

They could simply "grin and bear" the awkwardness for a few months and stick to their announced release schedule.

Alternatively, they could ultimately overhaul their Windows 10 (and therefore their Office 365, and maybe even their Windows 10 Server) Servicing Model.

I will discuss the potential outcomes in a minute, but before I get to that, I want to talk about the "why" first.

Microsoft Aims To Get Enterprises On Board With Support Extension

It has been more than two-and-a-half years since Microsoft released Windows 10, its Windows-as-a-Service OS. Thanks to a free upgrade option and tremendous security improvements natively baked into the OS, adoption has been faster than any other operating system in Microsoft's history.

Nevertheless, enterprise adoption has been slower than the software giant had hoped for — partially due to the constant changes and confusion around the update release and end-of-life dates, branching/servicing name changes and deletions (I am looking at you, Current Branch for Business), as well as a change of pace in its feature update frequency to better align with the Office 365 release cycle.

However, gaining fast enterprise adoption is not only crucial for its cash cow Windows but necessary for the company's entire X-as-a-Service strategy. If large organizations refuse to (or simply cannot manage to) hop on the bi-annual update bandwagon, Microsoft has a big problem.

Windows-as-a-Service Requires A Different Servicing Management Model Than Any Other Windows OS Before

Constant confusion aside, there is an even more profound reason why Microsoft is struggling to get enterprises to adopt Windows-as-a-Service. Microsoft is asking businesses to entirely depart from the way they have managed Windows updates before and choose a new, more agile way of managing their operating systems.

I recently had an interesting chat with Rob Helm, the Managing Vice President of Directions on Microsoft, responsible for overseeing Microsoft's product roadmap and corporate organization for the analyst company. Here is his opinion:

Microsoft is driving customers to a faster rate of roll outs and telling them that to support it, they have to roll out completely new technology for deploying and managing Windows.

For example, they should use Autopilot rather than their standard imaging technologies they have used for Windows 7, Intune Microsoft hosted mobile device management service instead of group policy and similar kinds of technologies and Windows Analytics instead of some of the tools they already have for monitoring systems and for taking inventory before a migration.

It’s generally encouraging them not to really test new versions the way they've had before, instead to roll them out in a slow pace through a series of successively larger groups until they've got the process entirely rolled out. And to do this at least every 18 months, probably more frequently. So, it's a complete change in the way organizations operate Windows."

Of course, you can roll out your Windows 10 updates using images and deployment rings just fine, but Microsoft's end-game is to get every enterprise user to get (and pay) for an:

The problem is that almost no organization, other than Microsoft, has fully adopted the "Modern Management agenda" as of now.

Microsoft's Windows 10 Servicing Options Going Forward

At this point, Microsoft has successfully delayed any need to make a change for at least another year or so. But they are still at a crossroad: Should they give into the cries of analysts and enterprise IT executives and slow down their pace? Or should they stick with it and keep on track for two updates a year?

In my opinion, Microsoft will not stray from their WaaS strategy very far — there is too much internally and financially is hinging on the market adopting this new X-as-a-Service mentality that pushes its cloud agenda, and has put them on a straight path to becoming the first "trillion-dollar company." Microsoft is now also the biggest security company in the world, and you cannot lead the pack when it comes to cyber security if you update your operating system only every two years or more.

On the other side, Microsoft is heavily dependent upon enterprise revenue! If larger organizations are not getting on board with their "Modern IT Management" agenda, they might have to slow down. "Microsoft might switch to releasing one feature update per year and extending their support window to 24 months — we will find out soon!" says Rob Helm.

What do you think will happen? Where are you with your Windows 10 plans? Please join the discussion in the comments below.

Barry is a co-founder of Juriba, where he is focused on using his experience in IT migration to help drive product strategy, pre-sales and service delivery. He is an experienced End User Services executive that has helped manage thousands of users, computers, applications and mailboxes to their next IT platform. He has saved millions of dollars for internal departments and customers alike through product, project, process and service delivery efficiency.